US3766294A - Imido alkylene substituted aromatic carbocyclic polymers - Google Patents
Imido alkylene substituted aromatic carbocyclic polymers Download PDFInfo
- Publication number
- US3766294A US3766294A US00156067A US3766294DA US3766294A US 3766294 A US3766294 A US 3766294A US 00156067 A US00156067 A US 00156067A US 3766294D A US3766294D A US 3766294DA US 3766294 A US3766294 A US 3766294A
- Authority
- US
- United States
- Prior art keywords
- imido
- radicals
- aromatic carbocyclic
- polymers
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title abstract description 31
- 125000002947 alkylene group Chemical group 0.000 title description 2
- 229920000620 organic polymer Polymers 0.000 abstract description 34
- 239000004793 Polystyrene Substances 0.000 abstract description 23
- 229920002223 polystyrene Polymers 0.000 abstract description 23
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 238000000465 moulding Methods 0.000 abstract description 7
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 4
- 239000002966 varnish Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 238000005392 polarisation enhancment during attached nucleus testing Methods 0.000 abstract 1
- -1 aromatic carbocyclic radicals Chemical class 0.000 description 98
- 239000000203 mixture Substances 0.000 description 38
- 150000003254 radicals Chemical class 0.000 description 38
- 125000003118 aryl group Chemical group 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 17
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 16
- 239000010408 film Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910015900 BF3 Inorganic materials 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SMQIAQVRHOQLKW-UHFFFAOYSA-N 1-(chloromethyl)pyrrole-2,5-dione Chemical compound ClCN1C(=O)C=CC1=O SMQIAQVRHOQLKW-UHFFFAOYSA-N 0.000 description 2
- BHPDNFUVYQFFNK-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrole-2,5-dione Chemical compound OCN1C(=O)C=CC1=O BHPDNFUVYQFFNK-UHFFFAOYSA-N 0.000 description 2
- AMCRWCGVJMQXMZ-UHFFFAOYSA-N 2-(2-chloroethyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound ClCCN1C(C2C(C1=O)CCC=C2)=O AMCRWCGVJMQXMZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000004653 anthracenylene group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940073584 methylene chloride Drugs 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940117958 vinyl acetate Drugs 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- NOSXUFXBUISMPR-UHFFFAOYSA-N 1-tert-butylperoxyhexane Chemical compound CCCCCCOOC(C)(C)C NOSXUFXBUISMPR-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- MHHGQWMCVNQHLG-UHFFFAOYSA-N 2-prop-2-enylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC=C)C(=O)C2=C1 MHHGQWMCVNQHLG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 235000019399 azodicarbonamide Nutrition 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000006849 chlorophenylene group Chemical group 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004989 dicarbonyl group Chemical group 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002863 poly(1,4-phenylene oxide) polymer Polymers 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Definitions
- the present invention relates to various imidoalkylene substituted aromatic carbocyclic organic polymers.
- the polyimides of the present invention can have at least one chemically combined M radical of the formula,
- R is a divalent organo radical selected from hydrocarbon radicals and halogenated hydrocarbon radicals
- R is a monovalent radical selected from hydrogen monovalent hydrocarbon radicals and halogenated monovalent hydrocarbon radicals.
- Radicals included by R are, for example, arylene radicals, such as phenylene, bisphenylene, naphthylene, anthrylene, etc., alkylene radicals, such as ethylene, trimethylene, tetramethylene, etc., halogenated arylene and alkylene radicals such as chlorophenylene, chloronaphthylene, chloroethylene, chlorotrimethylene, etc.; aliphatically unsaturated radicals, such as 3,766,294 Patented Oct. 16, 1973 "ice where X is a radical selected from hydrogen, lower alkyl, halogen, or mixtures thereof, such as chloro, methyl, ethyl, propyl, bromo, etc.
- arylene radicals such as phenylene, bisphenylene, naphthylene, anthrylene, etc.
- alkylene radicals such as ethylene, trimethylene, tetramethylene, etc.
- Monovalent and hydrocarbon radicals included by R are, for example, phenyl, chlorophenyl, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc.
- R" is a polyvalent aromatic organo radical selected from M-substituted aromatic carbocyclic organo radicals selected from hydrocarbon radicals and halogenated hydrocarbon radicals, and a mixture of such M-substituted aromatic carbocyclic radicals, and other polyvalent organo radicals free of M-substitution selected from hydrocarbon radicals and halogenated hydrocarbon radicals
- Z is a polyvalent connective
- a is a whole number having a value of 0 or 1
- n is an integer equal to 2 to 1,000 inclusive, and preferably 5 to 500 inclusive.
- Radicals included by R of Formula 2 are selected from (a) M-substituted aromatic carbocyclic radicals having from 6 to 18 carbon atoms selected from hydrocarbon radicals and halogenated hydrocarbon radicals,
- (c) a mixture of (a), or (a) and (b) radicals, and polyvalent aliphatic radicals selected from hydrocarbon radicals and halogenated hydrocarbon radicals, where the (a) or (a) and (b) radicals are present in the mixture in an amount which is suflicient to provide for at least about 1 mole percent of (a) radicals based on the total moles of radicals in (c).
- Polyvalent connectives included by Z of Formula 2 are, for example,
- the imido-substituted aromatic carbocyclic organic polymers of the present invention also include M-substituted polymers of the formula,
- Z is a divalent organo connective such as,
- Q is a polyvalent aliphatic, radical derived from aliphatically saturated monovalent hydrocarbon radicals and halogenated hydrocarbon radicals
- W is a monovalent radical selected from hydrogen, alkyl radicals,- halogen radicals, aliphatic ester radicals, aromatic ester radicals, amido radicals, nitrile radicals, and aliphatic nitrile radicals.
- carbocyclic radicals included by R" of Formula 2 there are phenylene, tolylene, xylylene, naphthylene, anthrylene, terphenylene, etc.; halogenated derivatives of such aromatic carbocyclic radicals; M-substituted derivatives of such aromatic carbocyclic radicals,
- aromatic imido-methylene compounds for example,
- R, and R are as previously defined and Y is a radical selected from hydroxy and halogen, such as chloro, bromo, fluoro, etc.
- imido-alkylene compounds of Formula 5 can be employed with aromatic carbocyclic organic polymers included by Formula 3 in the presence of a Friedel-Crafts catalyst, such asboron tri-fiuoride to produce pendant aromatic carbocyclic polymers having at least one chemically-combined imido radical of the formula,
- M radical referred to hereinafter as an M radical, where all of the terms are shown in Formula 5.
- R' can be a mixture of aromatic carbocyclic radicals and imido-substituted aromatic carbocyclic radicals are substituted with M radicals in place of M radicals.
- Also taught in our above-mentioned copending application is a method for introducing imido-alkylene substitution in a variety of backbone polymers, structurally similar to polymers of Formula 2 to provide for a variety of imido-substituted polyaryleneoxides, polyarylene esters, polyarylene carbonates and polyamides, as respectively shown by F. Holub and C. Emerick Ser. No. 838,316, now Pat. 3,652,710, F. Holub and M. Evans Ser. No. 838,314, now Pat. 3,652,716, Ser. No. 838,306, now Pat. 3,652,715, Ser. No. 838,315, all of which have been filed on July 1, 1969, and assigned to the same assignee as the present invention.
- imido-alkylene substituted polystyrenes poly(ot-methylstyrene), polymethyl(a-methylstyrene), poly(dimethylstyrene), poly(chlorostyrene), poly(dichlorostyrene), styrene copolymers with butadiene, acrylonitrile, methylmethacrylate, vinylidenechloride, maleic anhydride, vinylchloride, vinylacetate, vinylamides, a-methylstyrene, etc.
- imido-methylene substituted aromatic carbocyclic polymers there also is included in the present invention imido-methylene substitutedaromatic carbocyclic polymers in the form of random copolymers, block polymers, and graft copolymers containing at least 10 mole percent of R" radicals or R' radicals as defined in Formulas 2 and 3.
- imido-methylene substituted polystyrene-polybutadiene graft copolymers etc.
- the imido-alkylene substituted aromatic organic polymer provided by the present invention can be employed in a variety of applications depending upon such factors as the type of aromatic organic polymer, the degree of imido-alkylene substitution in the polymer, and whether the imido-alkylene radicals, as shown by Formulas 1 and 6, are aliphatically unsaturated, or free of aliphatic unsaturation.
- aromatic organic polymers are substituted with imido-alkylene radicals of Formulas 1 and 6 which are free of aliphatic unsaturation, such aromatic organic polymers can provide for solvent-resistant coating compounds, molding resins, high temperature and oxidatively stable fibers and films, etc.
- the imido-alkylene substituted aromatic organic polymers of the present invention can be blended with various aliphatically unsaturated organic materials, such as aliphatically unsaturated organic monomers and certain aliphatically unsaturated organic polymers as well as organic polymers free of aliphatic unsaturation. Blends of the imidoalkylene substituted aromatic organic polymers and the aforementioned organic monomers or polymers can be made over a wide proportion by weight. Experience has shown that there should be employed at least about 5 percent, by weight, of the imido-alkylene substituted aromatic organic polymer to provide for cured products having improved characteristics.
- the blend of the imido-alkylene substituted aromatic polymer with the aforementioned organic materials can be employed in making laminating compounds, solventless varnishes, molding compounds, coating compositions, etc., depending upon the proportions of the imido-aliphatically unsaturated imido-alkylene substituted aromatic organic polymer and the organic polymer or monomer utilized in the blend.
- organic polymers that can be employed in combination with the imido-alkylene substituted aromatic organic polymers of the present invention are, for example, polyvinylphthal
- polyethylene polypropylene, polysulfones, polystyrene,
- Cure of the imido-alkylene substituted aromatic organic polymer, or blend thereof with any of the aforementioned organic monomers or polymers, or combination thereof can be effected with conventional free radical initiators at temperatures of from 50 C. to 300. C., while 100 C. to 200 C. has sometimes been found to be more desirable.
- Acceleration of the cure of the imido-alkylene substituted aromatic organic polymer, or blend thereof, can be achieved with organic peroxides, such as .dicumyl peroxide, benzoyl peroxide, tertiary butylperbenzoate, tertiary alkylperoxycarbonate, etc.'The peroxides canbe employed from about 0.1 percent to about percent by weight, based on the total weight of the blend.
- high temperature radical sources can also be employed, such as the commercially available azodicarbon amides, 2,5-dimethyl, -2,5-bis(tert-butylperoxyhexane), etc.
- the imido-al'kylene substituted aromatic polymers or blends thereof in addition to being curable by the aforementioned free radical initiators, can ,be cured with heat or radiation with high energy electrons,
- ganic polymers of the presentinvention there can be employed, by weight, fillers in proportions of from 0 to 200 parts of filler, per 100 parts of the imido-alkylene substituted aromatic organic polymer. Included among.
- fillers which can be employed are, for example, clay,
- ingredients such as solvents at from 60 percent to 90 percent by weight of the resulting curable composition also can be employed such as N-methyl pyrrolidone, dimethylacetamide, toluene, methylenechloride, as well as plasticizers such as trioctylphthalate, etc.
- the product which showed a strong carbonyl absorption at 1,720 cm.- the product was identified as a maleimidomethylene substituted polystyrene having about 25 mole percent of thephenyl radicals substituted with maleimidomethylene radicals based on the total moles of imido-substituted and unsubstituted phenyl radicals in the polystyrene.
- the identity of the polymer and the degree of substitution was further confirmed by ele- 7 mental analysis.
- a thin film of the product containing about 1 percent of benzophenone was subjected to ultraviolet irradiation for 20 seconds. Those parts of the film that were exposed to the ultraviolet light were found to be insoluble in organic solvents. The product is usefulas a photoresist.
- EXAMPLE 4 Boron trifluoride is slowly introduced into; a 10 percent solution of styrene-butadiene copolymer and N-chloromethylmaleimide in chlorobenzene.
- the styrene-butadiene copolymer is prepared in accordance with the method of Amos et al., US. Pat. 2,694,692 utilizing a mixture of 90 mole percent of butadiene and 10 mole percentof styrene.
- the N-chloromethylmaleimide is present in the mixture at about an equal molar amount of the styrene utilizedin making the copolymer.
- Thev solution is stirred.
- the product is a styrene-butadi'en'e copolymer having chemically combined styrylradicals substituted with maleimidomethylene radicals.
- a solution of the maleimidomethylene substituted polymer in chlorobenzene is poured onto an aluminum sub- 7 strate and the solvent is allowed to evaporate at a temperature below its boiling point.
- the resulting film containing about 2 percent by weight of, benzophenone is irradiated with ultraviolet light for a period of about 2 minutes.
- the film is found to be insoluble in chlorobenzene andexhibits valuable dielectric and insulating prop erties.
- a mixture was made of,2.5 parts of a polystyrene hava ing a molecular weight of about 100,000, 2 partsof N-(2- chloroethyl)tetrahydrophthalimide and 35 parts of anhywhere MQ is a tetrahydrophthalimidoethyl radical, which are chemically combined with about 75 mole percent of styrene units of the formula,
- a film of the imido-substituted polystyrene is cast from a tetrachloroethane solution onto an aluminum substrate.
- the film is exposed to fi-radiation to a dosage of 50 mr. It is found to be insoluble in several organic solvents including tetrachlorethane and useful as an organic solvent resistant coating.
- EXAMPLE 6 There was added to a solution of 2 parts of polystyrene in about 50 parts'of chloroform, 2 parts of N-hydroxymethylhexachloro--norbornene-2,3-dicarboxylic imide in the presence of boron trifluoride, which was employed at up to saturation in the mixture. The mixture was agitated at room temperature for about 4 hours. A product was recovered by addition to methanol, which was in the form of a colorless polymer showing strong carbonyl absorption at 1720 cm.- Based on method of preparation, the product was a polystyrene having phenyl radicals substituted with hexachloro 5 norbornene 2,3 dicarbonyl imidomethyl radicals. The polymer was cast onto a film from chloroform, which was converted to the insoluble state when exposed to ultraviolet light for about 20 seconds as described previously in the presence of a 1% by weight benzophenone photoinitiator.
- EXAMPLE 7 There was added to a solution of 1 part of a polychloro styrene, EXP-MX4616 from Dow Chemical Company, in about 10 parts of chloroform, 0.24 part of N-hydroxymethylmaleimide. Boron trifluoride was passed into the resulting mixture at room temperature with stirring. Upon effecting a detectable increase in viscosity of the solution, methanol was added in an amount to effect the precipitation of product. Based on method of preparation, the product was a maleimidomethyl substituted polychlorostyrene. Elemental analysis of the product showed that it contained about 6 mole percent of maleimidomethyl substituted phenyl radicals.
- a film of the product was cast from a chloroform solution containing a 1% concentration of benzophenone. There was obtained a film exhibiting a substantial increase in solvent resistance when it was exposed to ultraviolet light for a period of about 20 seconds. This established that the imido-substituted polystyrene could be employed as a photoresist.
- EXAMPLE 8 There is added 2 parts of boron trifluoride to a solution at room temperature of 10.4 parts of polystyrene and 1.3 parts of N-hydroxymethyl maleimide, dissolved in about 20 parts of methylene chloride and 30 parts of nitromethane. A product is obtained by pouring the resulting mixture into methanol after it is stirred for about fifteen hours. The product is dried in vacuo at 50 C. Based on method of preparation, the product is a maleimidomethyl substituted polystyrene.
- the above maleimidomethyl substituted polystyrene is blended with equal parts by weight of poly(2,6-dimethylphenyleneoxide) having a molecular weight of about 50,- 000.
- a finished structure is obtained when the blend is mloded at a temperature of about ISO-200 C. for about 60 minutes.
- the part exhibits valuable solvent resistance and can be employed in making automobile components requiring high performance.
- EXAMPLE 9 A solution of the above described maleimidomethyl substituted polystyrene is prepared by blending 1 part of the polystyrene with 9 parts of styrene monomer. There is added to the solution, 1% by weight of benzoyl peroxide. The resulting composition is poured into a mold and heated at C. for about 6 hours. There is obtained a finished reproduction of the mold. The part exhibits valuable solvent resistant properties.
- a film forming aromatic carbocyclic organic polymer which can be employed as a molding resin, or solvent resistant coating compound, which consists essentially of from 5 to 500 chemically combined units selected from the group consisting of,
- R is a divalent organo radical free of aliphatic unsaturation selected from the group consisting of hydrocarbon radicals and halogenated hydrocarbon radicals
- R is selected from the group consisting of hydrogen, monovalent hydrocarbon radicals and halogenated monovalent hydrocarbon radicals
- R' is a monovalent organo radical selected from the group consisting of hydrocarbon radicals or halogenated radicals
- b is an integer having'a value of from l to 4;inclusive,” and Z
- 1 "unsaturated-hydrocarhon radical, R'cis selected from the, is adivalent organo radical having'the formula I group;consistingrofhydrogen; 'monovalentihydrocarbon X X X 1 1 i radicals and halogenated monovalent' hydrocarbon radi-Z cals
- R",f is a rnonovalent organo radical selected from the 7 I 5 group consistin of hydrocarbon radicals or
- composition in accordance with claim 1 where the 7 V a 1 film forming'aromatic carbocyclic organic polymer is an 10 1 l X imido alkyl substituted halogenated polystyrene. 7 1 I 1 J 1 l 3.
- An imido-methylene substituted styrene butadiene and X is a radical selected from thet'group consisting of copolyrner in accordance with clair' nlll 1 hydrogen, alkyl, and mixiures thereof: 1
Abstract
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4092300A (en) * | 1973-02-05 | 1978-05-30 | General Electric Company | Polyamide acid salts |
US4283509A (en) * | 1978-02-08 | 1981-08-11 | Ciba-Geigy Corporation | Photocrosslinkable polymers with side tricyclic imidyl groups |
US4448906A (en) * | 1982-06-16 | 1984-05-15 | Nuodex Inc. | Surface-coating compositions |
-
1971
- 1971-06-23 US US00156067A patent/US3766294A/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4092300A (en) * | 1973-02-05 | 1978-05-30 | General Electric Company | Polyamide acid salts |
US4283509A (en) * | 1978-02-08 | 1981-08-11 | Ciba-Geigy Corporation | Photocrosslinkable polymers with side tricyclic imidyl groups |
US4377669A (en) * | 1978-02-08 | 1983-03-22 | Ciba-Geigy Corporation | Photocrosslinkable polyester with side tricyclic imidyl groups |
US4377668A (en) * | 1978-02-08 | 1983-03-22 | Ciba-Geigy Corporation | Photo-crosslinkable polyamide with side tricyclic imidyl groups |
US4448906A (en) * | 1982-06-16 | 1984-05-15 | Nuodex Inc. | Surface-coating compositions |
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